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dc.contributor.authorMilner, Phillip John
dc.contributor.authorKinzel, Tom
dc.contributor.authorZhang, Yong
dc.contributor.authorBuchwald, Stephen Leffler
dc.date.accessioned2015-11-02T18:49:21Z
dc.date.available2015-11-02T18:49:21Z
dc.date.issued2014-10
dc.date.submitted2014-09
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126
dc.identifier.urihttp://hdl.handle.net/1721.1/99657
dc.description.abstractIsotopic labeling has been used to determine that a portion of the desired product in the Pd-catalyzed fluorination of electron-rich, non-ortho-substituted aryl triflates results from direct C–F cross-coupling. In some cases, formation of a Pd-aryne intermediate is responsible for producing undesired regioisomers. The generation of the Pd-aryne intermediate occurs primarily via ortho-deprotonation of a L·Pd(Ar)OTf (L = biaryl monophosphine) species by CsF and thus competes directly with the transmetalation step of the catalytic cycle. Deuterium labeling studies were conducted with a variety of aryl triflates.en_US
dc.description.sponsorshipNational Institutes of Health (U.S.) (Award GM46059)en_US
dc.description.sponsorshipNational Science Foundation (U.S.) (Predoctoral Fellowship 2010094243)en_US
dc.description.sponsorshipAmgen Inc.en_US
dc.description.sponsorshipAlexander von Humboldt-Stiftung (Feodor Lynen Postdoctoral Fellowship)en_US
dc.language.isoen_US
dc.publisherAmerican Chemical Society (ACS)en_US
dc.relation.isversionofhttp://dx.doi.org/10.1021/ja509144ren_US
dc.rightsArticle is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.en_US
dc.sourceACSen_US
dc.titleStudying Regioisomer Formation in the Pd-Catalyzed Fluorination of Aryl Triflates by Deuterium Labelingen_US
dc.typeArticleen_US
dc.identifier.citationMilner, Phillip J., Tom Kinzel, Yong Zhang, and Stephen L. Buchwald. “Studying Regioisomer Formation in the Pd-Catalyzed Fluorination of Aryl Triflates by Deuterium Labeling.” Journal of the American Chemical Society 136, no. 44 (November 5, 2014): 15757–15766. © 2014 American Chemical Societyen_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistryen_US
dc.contributor.mitauthorMilner, Phillip Johnen_US
dc.contributor.mitauthorKinzel, Tomen_US
dc.contributor.mitauthorZhang, Yongen_US
dc.contributor.mitauthorBuchwald, Stephen Leffleren_US
dc.relation.journalJournal of the American Chemical Societyen_US
dc.eprint.versionFinal published versionen_US
dc.type.urihttp://purl.org/eprint/type/JournalArticleen_US
eprint.statushttp://purl.org/eprint/status/PeerRevieweden_US
dspace.orderedauthorsMilner, Phillip J.; Kinzel, Tom; Zhang, Yong; Buchwald, Stephen L.en_US
dc.identifier.orcidhttps://orcid.org/0000-0003-3875-4775
dspace.mitauthor.errortrue
mit.licensePUBLISHER_POLICYen_US
mit.metadata.statusComplete


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